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Antimycin A3

Antimycin A3

  • CAT Number: I011419
  • CAS Number: 522-70-3
  • PubChem Substance ID: 245869
  • Molecular Formula: C26H36N2O9
  • Molecular Weight: 520.579
  • Purity: ≥95%
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Antimycin A3(CAT: I011419) is a naturally occurring antibiotic and mitochondrial electron transport inhibitor. It belongs to the antimycin class of compounds and is derived from the fermentation of certain Streptomyces bacteria. Antimycin A3 exerts its pharmacologic action by binding to complex III (cytochrome bc1 complex) in the mitochondrial respiratory chain, disrupting electron transfer and inhibiting oxidative phosphorylation. This disruption leads to a decrease in ATP synthesis and an accumulation of reactive oxygen species. Antimycin A3 is commonly employed as a research tool to investigate mitochondrial function, oxidative stress, and cellular metabolism. It is also used in agricultural settings to control plant pathogens and as a piscicide in fish management programs.

Catalog Number I011419
CAS Number 522-70-3
Molecular Formula

C26H36N2O9

Purity 95%
Storage -20°C
Related CAS 1362-89-6;11011-32-8
IUPAC Name [(2R,3S,6S,7R,8R)-8-butyl-3-[(3-formamido-2-hydroxybenzoyl)amino]-2,6-dimethyl-4,9-dioxo-1,5-dioxonan-7-yl] 3-methylbutanoate
InChI InChI=1S/C26H36N2O9/c1-6-7-9-18-23(37-20(30)12-14(2)3)16(5)36-26(34)21(15(4)35-25(18)33)28-24(32)17-10-8-11-19(22(17)31)27-13-29/h8,10-11,13-16,18,21,23,31H,6-7,9,12H2,1-5H3,(H,27,29)(H,28,32)/t15-,16+,18-,21+,23+/m1/s1
InChIKey PVEVXUMVNWSNIG-PDPGNHKXSA-N
SMILES CCCCC1C(C(OC(=O)C(C(OC1=O)C)NC(=O)C2=C(C(=CC=C2)NC=O)O)C)OC(=O)CC(C)C
Reference

<span style=”color:#000000;”><span style=”font-family:arial,helvetica,sans-serif;”><span style=”font-size:12px;”>1.Yonehara H. &amp; Takeuchi S. J.&nbsp;Studies on the chemical structure of blastmycin. Antibiotics Ser. A 11, 254 (1958).</span></span></span><br />
<span style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0);”>2.</span><span class=”authors” data-text=”Barrow, C.J., Oleynek, J.J., Marinelli, V., et al.” style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); box-sizing: border-box; font-variant-ligatures: normal; orphans: 2; widows: 2;”><span style=”box-sizing: border-box;”><span class=”scientificMarkup” style=”box-sizing: border-box;”>Barrow, C.J., Oleynek, J.J., Marinelli, V.,&nbsp;<span class=”foreign” style=”box-sizing: border-box; font-style: italic;”>et al</span>.</span></span></span><span class=”title” data-text=”Antimycins, inhibitors of ATP-citrate lyase, from a Streptomyces sp.” style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); box-sizing: border-box; font-variant-ligatures: normal; orphans: 2; widows: 2;”>&nbsp;<span style=”box-sizing: border-box;”><span class=”scientificMarkup” style=”box-sizing: border-box;”>Antimycins, inhibitors of ATP-<wbr style=”box-sizing: border-box;” />citrate lyase, from a&nbsp;<span class=”species” style=”box-sizing: border-box; font-style: italic;”>Streptomyces</span>&nbsp;sp.</span></span></span><span class=”journal” style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); box-sizing: border-box; font-style: italic; font-variant-ligatures: normal; orphans: 2; widows: 2;”>&nbsp;J. Antibiot. (Tokyo)</span><span class=”number” style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); box-sizing: border-box; font-weight: 700; font-variant-ligatures: normal; orphans: 2; widows: 2;”>&nbsp;</span><span class=”pagerange” style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); box-sizing: border-box; font-variant-ligatures: normal; orphans: 2; widows: 2;”>50(9), 729-733</span><span class=”year” style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); box-sizing: border-box; font-variant-ligatures: normal; orphans: 2; widows: 2;”>&nbsp;(1997)</span><span style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); font-variant-ligatures: normal; orphans: 2; widows: 2;”>.</span><br />
<span style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); font-variant-ligatures: normal; orphans: 2; widows: 2;”>3.</span><span class=”authors” data-text=”Takimoto, H., Machida, K., Ueki, M., et al.” style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); box-sizing: border-box; font-variant-ligatures: normal; orphans: 2; widows: 2;”><span style=”box-sizing: border-box;”><span class=”scientificMarkup” style=”box-sizing: border-box;”>Takimoto, H., Machida, K., Ueki, M.,&nbsp;<span class=”foreign” style=”box-sizing: border-box; font-style: italic;”>et al</span>.</span></span></span><span class=”title” data-text=”UK-2A, B, C and D, novel antifungal antibiotics from Streptomyces sp. 517-02 IV. Comparative studies of UK-2A with antimycin A3 on cytotoxic activity and reactive oxygen species generation in LLC-PK1 cells” style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); box-sizing: border-box; font-variant-ligatures: normal; orphans: 2; widows: 2;”>&nbsp;<span style=”box-sizing: border-box;”><span class=”scientificMarkup” style=”box-sizing: border-box;”>UK-<wbr style=”box-sizing: border-box;” />2A, B, C and D, novel antifungal antibiotics from&nbsp;<span class=”species” style=”box-sizing: border-box; font-style: italic;”>Streptomyces</span>&nbsp;sp. 517-<wbr style=”box-sizing: border-box;” />02 IV. Comparative studies of UK-<wbr style=”box-sizing: border-box;” />2A with antimycin A<sub style=”box-sizing: border-box; position: relative; font-size: 12px; line-height: 0; bottom: -0.25em;”>3</sub>&nbsp;on cytotoxic activity and reactive oxygen species generation in LLC-<wbr style=”box-sizing: border-box;” />PK1 cells</span></span>.</span><span class=”journal” style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); box-sizing: border-box; font-style: italic; font-variant-ligatures: normal; orphans: 2; widows: 2;”>&nbsp;J. Antibiot. (Tokyo)</span><span class=”number” style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); box-sizing: border-box; font-weight: 700; font-variant-ligatures: normal; orphans: 2; widows: 2;”>&nbsp;</span><span class=”pagerange” style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); box-sizing: border-box; font-variant-ligatures: normal; orphans: 2; widows: 2;”>52(5),480-484</span><span class=”year” style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); box-sizing: border-box; font-variant-ligatures: normal; orphans: 2; widows: 2;”>&nbsp;(1999)</span><span style=”font-family: arial, helvetica, sans-serif; color: rgb(0, 0, 0); font-variant-ligatures: normal; orphans: 2; widows: 2;”>.</span>

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